NZ223432A - Amino and or peptide substituted pyridine 2,4 and 2,5 dicarboxylic and derivatives and medicaments - Google Patents
Amino and or peptide substituted pyridine 2,4 and 2,5 dicarboxylic and derivatives and medicamentsInfo
- Publication number
- NZ223432A NZ223432A NZ223432A NZ22343288A NZ223432A NZ 223432 A NZ223432 A NZ 223432A NZ 223432 A NZ223432 A NZ 223432A NZ 22343288 A NZ22343288 A NZ 22343288A NZ 223432 A NZ223432 A NZ 223432A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- amino acid
- pyridine
- collagen
- compound
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims abstract description 13
- 108090000765 processed proteins & peptides Proteins 0.000 title description 2
- 150000003222 pyridines Chemical class 0.000 title description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 16
- 108010035532 Collagen Proteins 0.000 claims abstract description 12
- 102000008186 Collagen Human genes 0.000 claims abstract description 12
- 229920001436 collagen Polymers 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 6
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- 230000004060 metabolic process Effects 0.000 claims abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000741 silica gel Substances 0.000 claims description 10
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- 102000004079 Prolyl Hydroxylases Human genes 0.000 claims description 9
- 108010043005 Prolyl Hydroxylases Proteins 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 102000008490 2-Oxoglutarate 5-Dioxygenase Procollagen-Lysine Human genes 0.000 claims description 6
- 108010020504 2-Oxoglutarate 5-Dioxygenase Procollagen-Lysine Proteins 0.000 claims description 6
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 3
- 239000003018 immunosuppressive agent Substances 0.000 claims description 3
- TYQYRKDGHAPZRF-INIZCTEOSA-N benzyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate Chemical compound O=C([C@H](CC=1C2=CC=CC=C2NC=1)N)OCC1=CC=CC=C1 TYQYRKDGHAPZRF-INIZCTEOSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 230000001861 immunosuppressant effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229940024606 amino acid Drugs 0.000 description 16
- 239000002253 acid Substances 0.000 description 10
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- -1 heterocyclic amines Chemical class 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102000004266 Collagen Type IV Human genes 0.000 description 3
- 108010042086 Collagen Type IV Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- MJIVRKPEXXHNJT-UHFFFAOYSA-L lutidinate(2-) Chemical compound [O-]C(=O)C1=CC=NC(C([O-])=O)=C1 MJIVRKPEXXHNJT-UHFFFAOYSA-L 0.000 description 3
- MJIVRKPEXXHNJT-UHFFFAOYSA-N lutidinic acid Chemical compound OC(=O)C1=CC=NC(C(O)=O)=C1 MJIVRKPEXXHNJT-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 229940127557 pharmaceutical product Drugs 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RNROEWLWTMHYHA-UHFFFAOYSA-N bis(4-nitrophenyl) pyridine-2,4-dicarboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)C1=CC=NC(C(=O)OC=2C=CC(=CC=2)[N+]([O-])=O)=C1 RNROEWLWTMHYHA-UHFFFAOYSA-N 0.000 description 2
- UZTCTGIQCRJCLG-UHFFFAOYSA-N bis(4-nitrophenyl) pyridine-2,5-dicarboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)C1=CC=C(C(=O)OC=2C=CC(=CC=2)[N+]([O-])=O)N=C1 UZTCTGIQCRJCLG-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000036570 collagen biosynthesis Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VPNIQGRFZCTBEZ-SPTGULJVSA-N 3-n-[(2s,3r)-4-(cyclopropylamino)-3-hydroxy-1-phenylbutan-2-yl]-5-[methyl(methylsulfonyl)amino]-1-n-[(1r)-1-phenylethyl]benzene-1,3-dicarboxamide Chemical compound C([C@H](NC(=O)C=1C=C(C=C(C=1)C(=O)N[C@H](C)C=1C=CC=CC=1)N(C)S(C)(=O)=O)[C@H](O)CNC1CC1)C1=CC=CC=C1 VPNIQGRFZCTBEZ-SPTGULJVSA-N 0.000 description 1
- JKTYGPATCNUWKN-UHFFFAOYSA-N 4-nitrobenzyl alcohol Chemical compound OCC1=CC=C([N+]([O-])=O)C=C1 JKTYGPATCNUWKN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000001187 Collagen Type III Human genes 0.000 description 1
- 108010069502 Collagen Type III Proteins 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000024781 Immune Complex disease Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 1
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
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- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 231100000644 Toxic injury Toxicity 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
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- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
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- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
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- 238000003556 assay Methods 0.000 description 1
- 229940076134 benzene Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- FPRSPUHXEPWUBZ-HNNXBMFYSA-N benzyl (2s)-2-amino-3-phenylpropanoate Chemical compound C([C@H](N)C(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 FPRSPUHXEPWUBZ-HNNXBMFYSA-N 0.000 description 1
- CEXFHIYDTRNBJD-RSAXXLAASA-N benzyl (2s)-2-amino-3-phenylpropanoate;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 CEXFHIYDTRNBJD-RSAXXLAASA-N 0.000 description 1
- MBRRYUQWSOODEO-LBPRGKRZSA-N benzyl (2s)-2-amino-4-methylpentanoate Chemical compound CC(C)C[C@H](N)C(=O)OCC1=CC=CC=C1 MBRRYUQWSOODEO-LBPRGKRZSA-N 0.000 description 1
- QTQGHKVYLQBJLO-YDALLXLXSA-N benzyl (2s)-2-amino-4-methylpentanoate;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC(C)C[C@H](N)C(=O)OCC1=CC=CC=C1 QTQGHKVYLQBJLO-YDALLXLXSA-N 0.000 description 1
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- NWICUTXAPRFWLK-UHFFFAOYSA-N benzyl 2-[(1-oxo-3-phenyl-1-phenylmethoxypropan-2-yl)amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1CC(NC(CC=1C=CC=CC=1)C(=O)OCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 NWICUTXAPRFWLK-UHFFFAOYSA-N 0.000 description 1
- ABWSUGKHRQKUJV-UHFFFAOYSA-N benzyl 3-(1H-indol-3-yl)-2-[[3-(1H-indol-3-yl)-1-oxo-1-phenylmethoxypropan-2-yl]amino]propanoate Chemical compound C=1NC2=CC=CC=C2C=1CC(NC(CC=1C2=CC=CC=C2NC=1)C(=O)OCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 ABWSUGKHRQKUJV-UHFFFAOYSA-N 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Bidet-Like Cleaning Device And Other Flush Toilet Accessories (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873703962 DE3703962A1 (de) | 1987-02-10 | 1987-02-10 | Pyridin-2,4- und 2,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ223432A true NZ223432A (en) | 1990-04-26 |
Family
ID=6320592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ223432A NZ223432A (en) | 1987-02-10 | 1988-02-08 | Amino and or peptide substituted pyridine 2,4 and 2,5 dicarboxylic and derivatives and medicaments |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4968670A (de) |
| EP (1) | EP0278454B1 (de) |
| JP (1) | JPS63216871A (de) |
| KR (1) | KR960004861B1 (de) |
| AT (1) | ATE85048T1 (de) |
| AU (1) | AU604293B2 (de) |
| CA (1) | CA1315471C (de) |
| DE (2) | DE3703962A1 (de) |
| DK (1) | DK168008B1 (de) |
| ES (1) | ES2046218T3 (de) |
| FI (1) | FI90767C (de) |
| GR (1) | GR3007607T3 (de) |
| HU (1) | HU199801B (de) |
| IE (1) | IE62353B1 (de) |
| IL (1) | IL85360A0 (de) |
| NO (1) | NO174852C (de) |
| NZ (1) | NZ223432A (de) |
| PH (1) | PH24512A (de) |
| PT (1) | PT86735B (de) |
| ZA (1) | ZA88895B (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3707429A1 (de) * | 1987-03-07 | 1988-09-15 | Hoechst Ag | Substituierte pyridin-2,4-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen |
| US5425289A (en) * | 1993-10-21 | 1995-06-20 | Snap-On Incorporated | Bung tool |
| DE3924093A1 (de) * | 1989-07-20 | 1991-02-07 | Hoechst Ag | N,n'-bis(alkoxy-alkyl)-pyridin-2,4-dicarbonsaeurediamide, verfahren zu deren herstellung sowie deren verwendung |
| DE3938805A1 (de) * | 1989-11-23 | 1991-05-29 | Hoechst Ag | Pyridin-2,4- und 2,5-dicarbonsaeurediamide, verfahren zu deren herstellung sowie deren verwendung |
| DE4020570A1 (de) | 1990-06-28 | 1992-01-02 | Hoechst Ag | 2,4- und 2,5-substituierte pyridin-n-oxide, verfahren zu deren herstellung sowie deren verwendung |
| DE4031000A1 (de) * | 1990-10-01 | 1992-04-09 | Hoechst Ag | 4- oder 5-substituierte pyridin-2-carbonsaeuren, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
| YU9492A (sh) * | 1991-02-05 | 1995-03-27 | Hoechst Ag. | 2,4- i 2,5-bis-tetrazolilni piridini i postupak za njihovo dobijanje |
| EP0548883A1 (de) * | 1991-12-24 | 1993-06-30 | Hoechst Aktiengesellschaft | Substituierte Pyridin-N-oxide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| TW352384B (en) * | 1992-03-24 | 1999-02-11 | Hoechst Ag | Sulfonamido- or sulfonamidocarbonylpyridine-2-carboxamides, process for their preparation and their use as pharmaceuticals |
| DE4233124A1 (de) * | 1992-10-02 | 1994-04-07 | Hoechst Ag | Acylsulfonamido- und Sulfonamidopyridin-2-carbonsäureester sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO1999021860A1 (en) * | 1997-10-24 | 1999-05-06 | Fibrogen, Inc. | Phenanthroline derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3432094A1 (de) * | 1984-08-31 | 1986-03-06 | Hoechst Ag, 6230 Frankfurt | Ester der pyridin-2,4- und -2,5- dicarbonsaeure als arzneimittel zur inhibierung der prolin- und lysinhydroxylase |
| EP0353668B1 (de) * | 1988-08-04 | 1994-10-19 | Hoechst Aktiengesellschaft | Verbessertes Verfahren zur Herstellung von N,N-Bis(alkoxyalkyl)-pyridin -2,4-dicarbonsäurediamiden |
-
1987
- 1987-02-10 DE DE19873703962 patent/DE3703962A1/de not_active Withdrawn
-
1988
- 1988-02-08 EP EP88101793A patent/EP0278454B1/de not_active Expired - Lifetime
- 1988-02-08 ES ES198888101793T patent/ES2046218T3/es not_active Expired - Lifetime
- 1988-02-08 DE DE8888101793T patent/DE3877778D1/de not_active Expired - Fee Related
- 1988-02-08 AT AT88101793T patent/ATE85048T1/de not_active IP Right Cessation
- 1988-02-08 US US07/153,440 patent/US4968670A/en not_active Expired - Fee Related
- 1988-02-08 FI FI880555A patent/FI90767C/fi not_active IP Right Cessation
- 1988-02-08 IL IL85360A patent/IL85360A0/xx not_active IP Right Cessation
- 1988-02-08 PH PH36468A patent/PH24512A/en unknown
- 1988-02-08 NZ NZ223432A patent/NZ223432A/en unknown
- 1988-02-09 JP JP63026722A patent/JPS63216871A/ja active Pending
- 1988-02-09 DK DK066188A patent/DK168008B1/da not_active IP Right Cessation
- 1988-02-09 AU AU11451/88A patent/AU604293B2/en not_active Ceased
- 1988-02-09 KR KR88001197A patent/KR960004861B1/ko active IP Right Grant
- 1988-02-09 IE IE35188A patent/IE62353B1/en not_active IP Right Cessation
- 1988-02-09 CA CA000558495A patent/CA1315471C/en not_active Expired - Fee Related
- 1988-02-09 ZA ZA880895A patent/ZA88895B/xx unknown
- 1988-02-09 PT PT86735A patent/PT86735B/pt not_active IP Right Cessation
- 1988-02-09 NO NO880557A patent/NO174852C/no unknown
- 1988-02-10 HU HU88611A patent/HU199801B/hu not_active IP Right Cessation
-
1993
- 1993-04-09 GR GR930400360T patent/GR3007607T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3703962A1 (de) | 1988-08-18 |
| NO880557L (no) | 1988-08-11 |
| AU1145188A (en) | 1988-08-11 |
| CA1315471C (en) | 1993-03-30 |
| NO174852C (no) | 1994-07-20 |
| FI90767C (fi) | 1994-03-25 |
| US4968670A (en) | 1990-11-06 |
| NO174852B (no) | 1994-04-11 |
| EP0278454A2 (de) | 1988-08-17 |
| KR880009934A (ko) | 1988-10-05 |
| DK66188A (da) | 1988-08-11 |
| DK168008B1 (da) | 1994-01-17 |
| DK66188D0 (da) | 1988-02-09 |
| ES2046218T3 (es) | 1994-02-01 |
| IE880351L (en) | 1988-08-10 |
| ZA88895B (en) | 1988-08-08 |
| HU199801B (en) | 1990-03-28 |
| HUT47251A (en) | 1989-02-28 |
| KR960004861B1 (en) | 1996-04-16 |
| PT86735B (pt) | 1992-05-29 |
| PT86735A (pt) | 1988-03-01 |
| ATE85048T1 (de) | 1993-02-15 |
| EP0278454A3 (en) | 1989-10-18 |
| AU604293B2 (en) | 1990-12-13 |
| FI880555A (fi) | 1988-08-11 |
| IE62353B1 (en) | 1995-01-25 |
| EP0278454B1 (de) | 1993-01-27 |
| IL85360A0 (en) | 1988-07-31 |
| NO880557D0 (no) | 1988-02-09 |
| JPS63216871A (ja) | 1988-09-09 |
| GR3007607T3 (de) | 1993-08-31 |
| DE3877778D1 (de) | 1993-03-11 |
| FI90767B (fi) | 1993-12-15 |
| FI880555A0 (fi) | 1988-02-08 |
| PH24512A (en) | 1990-07-18 |
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